Triethylamine → HCID 67727699, compound

HRID 963049Notes

Reaction equation

HRID 963049 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16]([OH:18])=O)=[O:5])[CH3:2].[NH2:19][CH2:20][C:21]1[N:25]2[C:26]3[S:40][C:39]([CH2:41][CH3:42])=[CH:38][C:27]=3[C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])=[N:29][CH2:30][C:24]2=[N:23][N:22]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:28]1[C:27]2[CH:38]=[C:39]([CH2:41][CH3:42])[S:40][C:26]=2[N:25]2[C:21]([CH2:20][NH:19][C:16]([C:8]3[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:15]4[C:10]([CH:9]=3)=[CH:11][CH:12]=[CH:13][CH:14]=4)=[O:18])=[N:22][N:23]=[C:24]2[CH2:30][N:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21942335HCID 21942335, compoundHCID 67727814HCID 67727814, compound

Product 1

HCID 67727699HCID 67727699, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethoxycarbonylmethylindole-2-carboxylic acid (1.36 g) synthesized by a known method such as the method described in Japanese Patent Unexamined Publication No. 279374/1991, 9-aminomethyl-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (1.79 g) and triethylamine (1.4 ml) were dissolved in dimethylformamide (15 ml). 1-Benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (Bop reagent, 2.43 g) was added at room temperature, and the mixture was stirred for one day. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was crystallized from ethanol and isopropyl ether to give 2.78 g of crude crystals. The crystals were recrystallized from ethanol to give 1.77 g of ethyl 2-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-ylmethylcarbamoyl)indole-1-acetate.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from ethanol and isopropyl ether
  6. customto give 2.78 g of crude crystals
  7. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-7ff656d063f0468784ac5ebd6713b204
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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